NPASS Compound

Structure

CID27643 OpenBabel06191715352D 25 26 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 11 1 0 0 0 0 4 14 2 0 0 0 0 5 9 1 0 0 0 0 5 15 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.15
Volume:	366.092
LogP:	4.653
LogD:	3.678
LogS:	-3.751
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	2.497
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	1.9666103980853222e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	100.11437225341797%
Volume Distribution (VD):	0.653
Pgp-substrate:	1.1502947807312012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.722
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.903
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	12.731
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.183
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.625
Maximum Recommended Daily Dose:	0.564
Skin Sensitization:	0.931
Carcinogencity:	0.731
Eye Corrosion:	0.003
Eye Irritation:	0.892
Respiratory Toxicity:	0.893

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC27643

Natural Product ID:	NPC27643
*Common Name:**	Licochalcone C
IUPAC Name:	(E)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	WBDNTJSRHDSPSR-KPKJPENVSA-N
Standard InCHI:	InChI=1S/C21H22O4/c1-14(2)4-11-18-20(24)13-8-16(21(18)25-3)7-12-19(23)15-5-9-17(22)10-6-15/h4-10,12-13,22,24H,11H2,1-3H3/b12-7+
SMILES:	COc1c(/C=C/C(=O)c2ccc(cc2)O)ccc(c1CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL141207
PubChem CID:	9840805
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Others	16

Activity Type	# Activity
Cell Line	4
Individual Protein	4
NON-MOLECULAR	1
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	30900.0	nM	PMID[552609]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	57000.0	nM	PMID[552610]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	26.0	%	PMID[552612]
NPT660	Cell Line	SW480	Homo sapiens	GI	=	25.0	%	PMID[552612]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	22.0	%	PMID[552612]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	1.0	%	PMID[552612]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	20.0	%	PMID[552612]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.42	n.a.	PMID[552613]
NPT841	Organism	Leishmania major	Leishmania major	Inhibition	=	93.8	%	PMID[552608]
NPT841	Organism	Leishmania major	Leishmania major	Inhibition	=	51.5	%	PMID[552608]
NPT841	Organism	Leishmania major	Leishmania major	Inhibition	=	20.7	%	PMID[552608]
NPT841	Organism	Leishmania major	Leishmania major	Inhibition	=	3.9	%	PMID[552608]
NPT27	Others	Unspecified		Inhibition	=	73.2	%	PMID[552608]
NPT27	Others	Unspecified		Inhibition	=	30.4	%	PMID[552608]
NPT27	Others	Unspecified		Inhibition	=	14.8	%	PMID[552608]
NPT27	Others	Unspecified		Inhibition	=	5.5	%	PMID[552608]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24000.0	nM	PMID[552611]
NPT2	Others	Unspecified		Inhibition	=	9.0	%	PMID[552612]
NPT2	Others	Unspecified		Inhibition	=	5.0	%	PMID[552612]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC27643 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	1490
0.2-0.3	3867
0.3-0.4	10463
0.4-0.5	7856
0.5-0.6	3483
0.6-0.7	6115
0.7-0.8	6306
0.8-0.85	1720
0.85-0.9	730
0.9-0.95	298
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC309717
0.9843	High Similarity	NPC189106
0.9843	High Similarity	NPC66384
0.9843	High Similarity	NPC112192
0.9843	High Similarity	NPC164236
0.9843	High Similarity	NPC128348
0.9769	High Similarity	NPC168105
0.9769	High Similarity	NPC66349
0.9769	High Similarity	NPC24394
0.9769	High Similarity	NPC477243
0.9769	High Similarity	NPC98115
0.9769	High Similarity	NPC150399
0.9769	High Similarity	NPC249606
0.9769	High Similarity	NPC477242
0.9769	High Similarity	NPC12165
0.9769	High Similarity	NPC186838
0.9769	High Similarity	NPC41461
0.9769	High Similarity	NPC25287
0.9769	High Similarity	NPC1486
0.9769	High Similarity	NPC274109
0.9769	High Similarity	NPC477244
0.9695	High Similarity	NPC472419
0.9695	High Similarity	NPC23870
0.9695	High Similarity	NPC153979
0.9695	High Similarity	NPC317119
0.9692	High Similarity	NPC131039
0.9692	High Similarity	NPC13575
0.9692	High Similarity	NPC156092
0.9685	High Similarity	NPC247779
0.9621	High Similarity	NPC21350
0.9615	High Similarity	NPC103842
0.9615	High Similarity	NPC286336
0.9549	High Similarity	NPC477956
0.9549	High Similarity	NPC470211
0.9549	High Similarity	NPC472366
0.9538	High Similarity	NPC175098
0.9538	High Similarity	NPC472365
0.9538	High Similarity	NPC263670
0.9538	High Similarity	NPC144051
0.9538	High Similarity	NPC56031
0.9538	High Similarity	NPC192304
0.9538	High Similarity	NPC242294
0.9538	High Similarity	NPC204960
0.9538	High Similarity	NPC28753
0.9538	High Similarity	NPC294593
0.9538	High Similarity	NPC312318
0.9538	High Similarity	NPC159623
0.9538	High Similarity	NPC337373
0.9538	High Similarity	NPC82225
0.9538	High Similarity	NPC18877
0.9538	High Similarity	NPC188646
0.9538	High Similarity	NPC20560
0.9538	High Similarity	NPC139813
0.9478	High Similarity	NPC172250
0.9478	High Similarity	NPC215311
0.9478	High Similarity	NPC213659
0.9478	High Similarity	NPC11056
0.9478	High Similarity	NPC259166
0.9478	High Similarity	NPC219917
0.9478	High Similarity	NPC48624
0.9478	High Similarity	NPC204985
0.9478	High Similarity	NPC144118
0.9478	High Similarity	NPC80962
0.9478	High Similarity	NPC326109
0.9474	High Similarity	NPC471620
0.9474	High Similarity	NPC251681
0.9474	High Similarity	NPC243528
0.9462	High Similarity	NPC212631
0.9462	High Similarity	NPC205468
0.9462	High Similarity	NPC257756
0.9462	High Similarity	NPC129132
0.9462	High Similarity	NPC87231
0.9407	High Similarity	NPC55832
0.9407	High Similarity	NPC268204
0.9407	High Similarity	NPC469404
0.9407	High Similarity	NPC321980
0.9407	High Similarity	NPC26051
0.9407	High Similarity	NPC52789
0.9407	High Similarity	NPC470087
0.9407	High Similarity	NPC110969
0.9407	High Similarity	NPC470089
0.9403	High Similarity	NPC283429
0.9403	High Similarity	NPC295384
0.9385	High Similarity	NPC262359
0.9385	High Similarity	NPC308037
0.9385	High Similarity	NPC313618
0.9385	High Similarity	NPC64359
0.9385	High Similarity	NPC186097
0.9385	High Similarity	NPC475008
0.9385	High Similarity	NPC475009
0.9338	High Similarity	NPC11561
0.9338	High Similarity	NPC226636
0.9333	High Similarity	NPC253822
0.9333	High Similarity	NPC172986
0.9333	High Similarity	NPC159275
0.9333	High Similarity	NPC69769
0.9333	High Similarity	NPC270883
0.9333	High Similarity	NPC241100
0.9333	High Similarity	NPC101366
0.9333	High Similarity	NPC261227
0.9328	High Similarity	NPC124269
0.9328	High Similarity	NPC472368
0.9323	High Similarity	NPC472364
0.9323	High Similarity	NPC476333
0.9323	High Similarity	NPC472367
0.9323	High Similarity	NPC473391
0.9323	High Similarity	NPC213603
0.9318	High Similarity	NPC164136
0.9313	High Similarity	NPC15834
0.9313	High Similarity	NPC215875
0.927	High Similarity	NPC18585
0.927	High Similarity	NPC475705
0.927	High Similarity	NPC117836
0.927	High Similarity	NPC105213
0.927	High Similarity	NPC310130
0.927	High Similarity	NPC166138
0.927	High Similarity	NPC91560
0.927	High Similarity	NPC75049
0.927	High Similarity	NPC106985
0.927	High Similarity	NPC39329
0.927	High Similarity	NPC143896
0.927	High Similarity	NPC257097
0.927	High Similarity	NPC301751
0.927	High Similarity	NPC245482
0.927	High Similarity	NPC169591
0.927	High Similarity	NPC68104
0.927	High Similarity	NPC175504
0.927	High Similarity	NPC150408
0.927	High Similarity	NPC149026
0.927	High Similarity	NPC164980
0.927	High Similarity	NPC51887
0.927	High Similarity	NPC476178
0.927	High Similarity	NPC221432
0.9265	High Similarity	NPC147688
0.9265	High Similarity	NPC64908
0.9265	High Similarity	NPC282300
0.9265	High Similarity	NPC26238
0.9265	High Similarity	NPC118840
0.9265	High Similarity	NPC103362
0.9265	High Similarity	NPC156590
0.9265	High Similarity	NPC3188
0.9265	High Similarity	NPC205006
0.9259	High Similarity	NPC53181
0.9259	High Similarity	NPC217186
0.9259	High Similarity	NPC96565
0.9259	High Similarity	NPC55018
0.9259	High Similarity	NPC216978
0.9259	High Similarity	NPC78913
0.9259	High Similarity	NPC18260
0.9259	High Similarity	NPC301217
0.9259	High Similarity	NPC220062
0.9259	High Similarity	NPC303633
0.9254	High Similarity	NPC7013
0.9254	High Similarity	NPC188879
0.9254	High Similarity	NPC303644
0.9254	High Similarity	NPC162680
0.9254	High Similarity	NPC294409
0.9254	High Similarity	NPC181124
0.9254	High Similarity	NPC116632
0.9254	High Similarity	NPC209560
0.9242	High Similarity	NPC16197
0.9231	High Similarity	NPC84772
0.9203	High Similarity	NPC473015
0.9203	High Similarity	NPC234629
0.9203	High Similarity	NPC328623
0.9203	High Similarity	NPC473013
0.9203	High Similarity	NPC471523
0.9203	High Similarity	NPC476055
0.9203	High Similarity	NPC197252
0.9203	High Similarity	NPC209040
0.9203	High Similarity	NPC157133
0.9203	High Similarity	NPC471524
0.9203	High Similarity	NPC311741
0.9203	High Similarity	NPC471473
0.9203	High Similarity	NPC236766
0.9197	High Similarity	NPC40833
0.9197	High Similarity	NPC148545
0.9197	High Similarity	NPC125855
0.9197	High Similarity	NPC161506
0.9197	High Similarity	NPC37496
0.9197	High Similarity	NPC78
0.9197	High Similarity	NPC166934
0.9197	High Similarity	NPC177354
0.9197	High Similarity	NPC194432
0.9197	High Similarity	NPC10937
0.9197	High Similarity	NPC148757
0.9197	High Similarity	NPC76338
0.9197	High Similarity	NPC1089
0.9197	High Similarity	NPC166482
0.9197	High Similarity	NPC227579
0.9197	High Similarity	NPC167624
0.9197	High Similarity	NPC144499
0.9197	High Similarity	NPC32739
0.9197	High Similarity	NPC265040
0.9197	High Similarity	NPC223500
0.9197	High Similarity	NPC328164
0.9197	High Similarity	NPC228504
0.9197	High Similarity	NPC182852
0.9197	High Similarity	NPC220998
0.9197	High Similarity	NPC324134

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC27643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	957
0.2-0.3	1422
0.3-0.4	2494
0.4-0.5	2027
0.5-0.6	1244
0.6-0.7	502
0.7-0.8	167
0.8-0.85	27
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9385	High Similarity	NPD1240	Approved
0.9242	High Similarity	NPD1607	Approved
0.9104	High Similarity	NPD1510	Phase 2
0.9065	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD7410	Clinical (unspecified phase)
0.8905	High Similarity	NPD1549	Phase 2
0.8832	High Similarity	NPD1550	Clinical (unspecified phase)
0.8832	High Similarity	NPD1552	Clinical (unspecified phase)
0.875	High Similarity	NPD4380	Phase 2
0.8705	High Similarity	NPD7421	Clinical (unspecified phase)
0.869	High Similarity	NPD7411	Suspended
0.8623	High Similarity	NPD2796	Approved
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.854	High Similarity	NPD6651	Approved
0.8523	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD6859	Clinical (unspecified phase)
0.8514	High Similarity	NPD8443	Clinical (unspecified phase)
0.8511	High Similarity	NPD3750	Approved
0.8489	Intermediate Similarity	NPD2935	Discontinued
0.8462	Intermediate Similarity	NPD6799	Approved
0.8446	Intermediate Similarity	NPD7819	Suspended
0.8446	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6801	Discontinued
0.8255	Intermediate Similarity	NPD1934	Approved
0.8243	Intermediate Similarity	NPD6599	Discontinued
0.8239	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7768	Phase 2
0.8212	Intermediate Similarity	NPD3882	Suspended
0.8207	Intermediate Similarity	NPD1511	Approved
0.82	Intermediate Similarity	NPD2801	Approved
0.8195	Intermediate Similarity	NPD3972	Approved
0.8194	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2800	Approved
0.8158	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD3748	Approved
0.8125	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1551	Phase 2
0.8095	Intermediate Similarity	NPD1512	Approved
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8056	Intermediate Similarity	NPD1243	Approved
0.8028	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2799	Discontinued
0.8027	Intermediate Similarity	NPD2532	Approved
0.8027	Intermediate Similarity	NPD2534	Approved
0.8027	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD9545	Approved
0.7937	Intermediate Similarity	NPD5953	Discontinued
0.7925	Intermediate Similarity	NPD7286	Phase 2
0.7925	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3749	Approved
0.7919	Intermediate Similarity	NPD920	Approved
0.7919	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2344	Approved
0.7891	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1203	Approved
0.7857	Intermediate Similarity	NPD3268	Approved
0.7852	Intermediate Similarity	NPD422	Phase 1
0.7848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6166	Phase 2
0.7848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6099	Approved
0.7847	Intermediate Similarity	NPD6100	Approved
0.7842	Intermediate Similarity	NPD4908	Phase 1
0.7826	Intermediate Similarity	NPD2798	Approved
0.7821	Intermediate Similarity	NPD5494	Approved
0.782	Intermediate Similarity	NPD1548	Phase 1
0.7815	Intermediate Similarity	NPD7458	Discontinued
0.7812	Intermediate Similarity	NPD5844	Phase 1
0.7808	Intermediate Similarity	NPD2654	Approved
0.78	Intermediate Similarity	NPD5403	Approved
0.7792	Intermediate Similarity	NPD3817	Phase 2
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7003	Approved
0.7754	Intermediate Similarity	NPD2797	Approved
0.775	Intermediate Similarity	NPD3818	Discontinued
0.773	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2313	Discontinued
0.7721	Intermediate Similarity	NPD1610	Phase 2
0.7718	Intermediate Similarity	NPD7390	Discontinued
0.7714	Intermediate Similarity	NPD6832	Phase 2
0.7703	Intermediate Similarity	NPD2309	Approved
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7681	Intermediate Similarity	NPD1876	Approved
0.7669	Intermediate Similarity	NPD9493	Approved
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7667	Intermediate Similarity	NPD5401	Approved
0.7664	Intermediate Similarity	NPD9717	Approved
0.7655	Intermediate Similarity	NPD4308	Phase 3
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.7606	Intermediate Similarity	NPD3764	Approved
0.7597	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7054	Approved
0.7591	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5124	Phase 1
0.7554	Intermediate Similarity	NPD3225	Approved
0.7546	Intermediate Similarity	NPD7472	Approved
0.7536	Intermediate Similarity	NPD1608	Approved
0.7535	Intermediate Similarity	NPD4625	Phase 3
0.7535	Intermediate Similarity	NPD3027	Phase 3
0.7534	Intermediate Similarity	NPD7033	Discontinued
0.7532	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7251	Discontinued
0.7453	Intermediate Similarity	NPD3926	Phase 2
0.7452	Intermediate Similarity	NPD4288	Approved
0.7452	Intermediate Similarity	NPD5402	Approved
0.7439	Intermediate Similarity	NPD1729	Discontinued
0.7438	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2346	Discontinued
0.7429	Intermediate Similarity	NPD1283	Approved
0.741	Intermediate Similarity	NPD7808	Phase 3
0.7402	Intermediate Similarity	NPD846	Approved
0.7402	Intermediate Similarity	NPD940	Approved
0.7394	Intermediate Similarity	NPD9494	Approved
0.7391	Intermediate Similarity	NPD3847	Discontinued
0.7391	Intermediate Similarity	NPD5711	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7386	Intermediate Similarity	NPD5049	Phase 3
0.7385	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4307	Phase 2
0.7376	Intermediate Similarity	NPD1470	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7361	Intermediate Similarity	NPD6798	Discontinued
0.7357	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2354	Approved
0.7343	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1201	Approved
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD17	Approved
0.7319	Intermediate Similarity	NPD4626	Approved
0.7305	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7284	Intermediate Similarity	NPD7229	Phase 3
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1613	Approved
0.726	Intermediate Similarity	NPD3142	Approved
0.726	Intermediate Similarity	NPD3140	Approved
0.726	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4476	Approved
0.7248	Intermediate Similarity	NPD4477	Approved
0.7241	Intermediate Similarity	NPD4361	Phase 2
0.7241	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3887	Approved
0.7234	Intermediate Similarity	NPD4749	Approved
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7215	Intermediate Similarity	NPD37	Approved
0.7214	Intermediate Similarity	NPD1281	Approved
0.7214	Intermediate Similarity	NPD1535	Discovery
0.7211	Intermediate Similarity	NPD6355	Discontinued
0.7211	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1933	Approved
0.7203	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2353	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD6104	Discontinued
0.7134	Intermediate Similarity	NPD5242	Approved
0.7125	Intermediate Similarity	NPD2296	Approved
0.7123	Intermediate Similarity	NPD411	Approved
0.7123	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD9268	Approved
0.7117	Intermediate Similarity	NPD7199	Phase 2
0.7108	Intermediate Similarity	NPD7177	Discontinued
0.7108	Intermediate Similarity	NPD5940	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data